Pharmaceutical compounds.



it, @TATE fiLBZi/ECHT THIELE, F BERLIN. GERMANY, ASSIGNOR TO CHEMISCHE FABRIK AU]? ACTIEN, (VDRM. E. SCHERING), OF BERLIN, GERMANY.

PHARMACEUTICAL COMPOUNDS.-

if-l $319,265.

No Drawing.

- :icicl substituted the benzol nucleus, the

molecule of which contains the following atomlc group:

Boos 7 2 i --1 income The new products are insoluble in Water unil have proved to he valuable ennlgetics, an average (lose being from '3 to 1 grain. They may he used as such or in the salt form.

The compounds can, for instance, be obtain-cal as follows, the parts being by weiqht:

(l) lilo parts of puratoluiilin are boiled i -a vessel with reflux comlenser for several hours with 150 parts of piperonal and 88 1 ms of pyroraceniio acid in alcoholic solulion. The i-nielhyl-Q-piperonylquinolin-4 cnrboizylic ucj. Scilill'tliQS out anal is purified through its sodium salt. It melts at about 2 3-2l7 eenirigreile anti i insoluble in Watcr s-ohibie in hot alcohol and has the following slructui'al formula:

Til parts pm'mninophenol are boiled for some time with 150 parts piperonal and 68 parts pjzrornceniic acid alcoholic solulion. E lie precipivaieal b-oxy-Z-piperoaiylqiiiriolin--cnrhoxj,*lic acid is purified. Eil'irough its sodium it insoluble in Specification of Letters Patent;

Patented M ay 30, 1916.

Application filed July 3, 1913. Serial No. 777,303.

waternnd soluble in alcohol melt at 300 centigrades.

(3) 1-10 parts orthoanisiclin are boiled for several hours with 150 pai'ts piperonal and 90 parts pyroracemic acid. The precipitated 8-methoxy-2-piperonylquinolin-4-carboxylic acid is twice precipitated out of its alkaline solution by means of an aciil and recrystallized out of 40 per cent. alcohol. The compound has a melting poinf of 114-415 centigrade and is insoluble in Water but soluble in alcohol.

I claim-as my invention 1. As new products'the Q-pipenmylquinolinA-carboxylic acid substituted in the benzol nucleus, the molecule of which con tains the following atomic group:

and does not COOH said products being the condensation products of pipcronal, pyroracemlc acid and derivatives from anlhn, such products being insoluble in water, forming salts and havinc analgetic properties, substantially as described.

2. As a new product the.(Fmetl1yh2-piperonylquinolin-el-carboxylic acid of the formula COOK our 5 4 ALBRPX'FHT 'lI-HELE. I

Nitness-es: v

HENRY HASPER,

WQLDEMAR HAUPT. 

